The Maddening Smile
by ravenbird13
Summary: The Mad Hatter wasn't always mad now was he? Jefferson left in Wonderland forced to create something he can't even hope to make, comes across someone who may just be able to help him - First chapter based before the Curse. I don't know if I will write anything during the curse. I don't have much inspiration for that. I hope anyone who reads likes it :) Possible Romance in the f
1. Chapter 1

**Chapter 1: The Meeting**

"Get it to work!...get it to work...GOT TO GET IT TO WORK!"

His voiced boomed in the room he had been trapped in, it shaking the large stacks of hats just barely. There were scattered all about, and all of different kinds. So many it was impossible to count. Some would think it would take years to make as many as there were, but he didn't even know how long he had been trapped there. In the god forsaken land of Wonderland. He continued though, furiously making hat after hat. With a slight spin of each once they were done, the Hatter quickly discarded of them while he continued to mumble or scream those same word 'get it to work.'

He was all alone there, or at least he should be. It started with a smile, large and sly. It bobbed and spun around some before something else appeared. Two eyes with a color that was indescribable, possible a strange mix of blue and green and from there the rest of a body began to appear bit by bit. It was a woman with that same smile spread on her lips. She soundlessly walked across the floor, looking at the tall stacks of hats. So many colors, so many to choose from. Finally she plucked one from the middle of the stack, and just like magic it didn't topple over. Trying it on, she quickly shook her head, "No, too big."

The mad man froze and slowly he turned. His eyes grew at the sight of the woman, for not only was she just pulling out the hats from the stacks like nothing but now she was floating. He tried to stand from his chair, but instead he fumbled, letting both himself and the chair clatter to the ground, grabbing the strange woman's attention.

"Ah, just the man I was looking for!" She beamed and she placed a certain green hat back. The woman soon began to drift toward the Hatter.

"No stay away! I do not want to deal with any more insane creatures...people...or whatever you are!" He yelled back at her.

She let out a soft laugh, the smile, now more of a smirk, was still present, "Oh that's impossible. After all we are all mad here, why even you are."

The man finally gained his feet again and he was fuming now, "I am not mad! I am not like any of you here! You are all the mad ones."

She simply ignored him, going off into a small tangent as she gazed down at what he was working on before the interruption, "Indeed you are mad, of course nothing compared to me. Granted everyone slips and slides. Mad you are for you are here. Only mad men talk to themselves, or constantly try and try again without changing anything, expecting a new result. None have worked yet. Am I right, Mad Hatter?"

Even as her words filled his head, the man wanted to deny their truth. What else could he do though! He had no magic, and the Queen surely wasn't going to give him any. He was stuck in this room day in and day out only being able to make hat after hat. And with each day, his guilt continued to build larger and larger. The man was pulled from his thoughts though, but the nickname that this woman dared to call him.

"Don't you dare call me that! That is not my name."

"Oh well then tell me, Hatter. What is your name?"

He stood silent for a moment, not sure whether to answer or not.

The man answered, "Jefferson."

"That's a charming name, Jefferson! I do like 'Mad Hatter' though, it would be so much better then if Tweedle dee and Tweedle dumb come up a name for you. So many strange names around here..."

Jefferson cut her off mid her tangent, " Well I told you mine. You might as well tell me yours! Especially since you interrupted my work."

"Oh forgive my rudeness, I must have forgotten my manners." She stated while she took a bow, using one hand to gesture to herself, "I am the Cheshire Cat."

Jefferson stared at the woman for a short time before retorting, "That isn't it a name!"

"It isn't? I sure thought it was my name. You know its been so long, I don't quite remember it. Perhaps it was Charles...no that doesn't seem right...what is even a name?.."

All he could do was stare at her, "You are absolutely mad, aren't you?"

"Oh I am not insane at all, my reality is just different from yours." She quickly answered before continuing speaking of names.

Why was this 'Cheshire Cat' even here? Jefferson questioned in his head. Something told him she was more insane than any other creature or person in this whole land. Cheshire was simply passing around a bit as she was going on a tangent once more, which happen to lead somewhere else. Suddenly Jefferson remembered something she said.

" You said I keep trying the same thing over and over again, but nothing is working."

"What isn't working?"

"My hats."

"These hats?"

"Yes these hats. None will open a portal."

"Why would you need a portal?"

"To get home!" Jefferson said with a sigh. He pinched the bridge of his nose in frustration.

Cheshire picked up a near top hat, having it spin upon her finger while the rest of her hand and arm disappeared. Quietly she whispered, "_Round and round the hat must go. Portals all around. Pick and choose from the doors of worlds. but beware those that go in must come out."_

"You want the hat to work as well?" Jefferson asked, grabbing Cheshire's attention. Those glass like eyes stared at him for so long, it almost made him tremble.

"Indeed. You are my way out, Hatter. Your problem is you got no magic and no way out this room. If you couldn't tell before, but I am not all here myself," She said as she slowly disappeared, the last remaining to be seen was the maddening grin of hers.

Jefferson looked every which way for her, except up. Cheshire slowly slinked her way back behind him, giving him a gently tap that made him jump. He knew that he would never get use to this woman.

"I bring things that you can try to use to help with this wonderful portal hat of yours, then if it works you take me with you. I don't care what land but anywhere from here." Cheshire said while trusting her hand out to him, "Deal?"

Jefferson looked at the extended hand thinking on the last deal he made with someone. That ended badly and it was the reason he was stuck here. Part of him wanted to refuse, but before he could second guess himself, Jefferson shook Cheshire's hand, "Deal."

"Wonderful." she said with a purr. Slowly she disappeared again, spiraling up from her legs she vanished. As always her smile remained longer than the rest. That to was hidden from sight when Jefferson blinked she was all gone.

**So I have always loved Once Upon a Time, at Jefferson is possibly one of my favorite characters, despite how little he is shown. Firstly I wan't to say that I have not seen the Wonderland spin off of OUaT, and I have no way of watching it. So not much, if at all, of that tv series will be shown. Sorry.**

**Anyway, I have had this character bouncing around in my head for a bit now, and really wanted to try my hand at writing. I am sorry, I'm quite new at writing. I have made any mistakes or if you have any suggestions please let me know in a review. I still hope you like this small chapter readers.**

**I am still not entirely sure how I want this to go. I am still deciding whether or not I will do it like the show (memory, present day, memory sequence). Or just do it from the beginning. Also there may be possible romance in the future.**


	2. revamp

**Basically I have decided I want to change the story a bit. I am not happy with how it is going right now and want to start over from the beginning of Cheshire's story. There will also be other ocs in it, cause come on there are hundreds upon hundreds of fairy tales out there, the possibilities for characters are endless. If anyone would like to see their ocs in this just let me know, I love writing characters besides my own.**

**It may be a week or longer before I update cause I still want to figure out if I want to do it like the tv series (Memory, present day, memory, present day) Or just go from the beginning to the end.**

**we shall see I guess**


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